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$48+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$82
(CheapOair)

One-way from

$48
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$255

Good round-trip deal

$170 or less

Good one-way deal

$169 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
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From Kentucky to Chicago (CHI)
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One-way flight from Kentucky to Chicago (CHI)
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
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Price to beat on a one-way flight from Kentucky to Chicago (CHI).
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Find flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:46 pmBNA - ORD
1 stop11h 00mFrontier
Mon 11/246:13 amORD - BNA
Nonstop1h 37mFrontier
Deal found 10/29$82
This Mytrip deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:00 pmBNA - ORD
Nonstop1h 50mMultiple Airlines
Thu 12/47:00 amORD - BNA
1 stop11h 46mMultiple Airlines
Deal found 10/29$91
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:20 pmSDF - ORD
Nonstop1h 38mUnited Airlines
Tue 12/97:55 pmORD - SDF
Nonstop1h 34mUnited Airlines
Deal found 10/30$97
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:45 amSDF - MDW
Nonstop1h 15mSouthwest
Mon 12/810:05 amMDW - SDF
Nonstop1h 25mSouthwest
Deal found 10/29$97
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:10 amBNA - MDW
Nonstop1h 45mSouthwest
Mon 12/812:25 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 10/29$97
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/811:19 amBNA - ORD
Nonstop1h 56mUnited Airlines
Mon 12/159:05 pmORD - BNA
Nonstop1h 44mUnited Airlines
Deal found 10/30$97
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:36 amBNA - ORD
Nonstop1h 55mAmerican Airlines
Mon 12/88:30 pmORD - BNA
Nonstop1h 50mAmerican Airlines
Deal found 10/29$98
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:49 pmBNA - ORD
Nonstop1h 48mFrontier
Mon 11/176:20 amORD - BNA
Nonstop1h 36mFrontier
Deal found 10/29$101
This Priceline deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:49 pmBNA - ORD
Nonstop1h 48mFrontier
Sun 11/166:10 pmORD - BNA
Nonstop1h 48mFrontier
Deal found 10/29$102
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/193:32 pmBNA - ORD
1 stop8h 55mMultiple Airlines
Mon 11/246:13 amORD - BNA
Nonstop1h 37mMultiple Airlines
Deal found 10/29$104
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/218:45 amBNA - ORD
Nonstop1h 53mFrontier
Mon 11/246:13 amORD - BNA
Nonstop1h 37mFrontier
Deal found 10/30$105
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:20 amBNA - ORD
Nonstop1h 55mSouthwest
Thu 12/116:05 amORD - BNA
1 stop5h 45mSouthwest
Deal found 10/28$107

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Kentucky

Fly to

Chicago

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 11/20

8:46 pm-7:46 am

1 stop11h 00m

Chicago O'Hare Intl

Mon 11/24

6:13 am-7:50 am

Nonstop1h 37m

$82

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 12/3

12:20 pm-12:58 pm

Nonstop1h 38m

Chicago O'Hare Intl

Tue 12/9

7:55 pm-10:29 pm

Nonstop1h 34m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 12/4

6:21 pm-7:16 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 12/8

8:20 pm-10:56 pm

Nonstop1h 36m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 12/4

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Mon 12/8

5:35 am-7:05 am

Nonstop1h 30m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 12/15

7:00 am-7:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Wed 12/17

9:05 am-11:32 am

Nonstop1h 27m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 12/8

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Thu 1/1

6:35 am-8:05 am

Nonstop1h 30m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 12/9

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Thu 12/11

8:30 pm-10:00 pm

Nonstop1h 30m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Mon 12/8

8:00 am-9:50 am

Nonstop1h 50m

Chicago O'Hare Intl

Wed 12/10

12:45 pm-2:28 pm

Nonstop1h 43m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 12/9

10:20 am-12:15 pm

Nonstop1h 55m

Chicago O'Hare Intl

Thu 12/11

6:05 am-11:50 am

1 stop5h 45m

$107

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 12/4

11:45 am-8:45 pm

2 stops10h 00m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, January is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $73). Flying from Kentucky to Chicago in July is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 32% on airfare.

What is the cheapest day to fly from Kentucky to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Kentucky to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kentucky to Chicago?

    There are many flights that can get you from Kentucky to Chicago in 1h 38m. Fly via Frontier, United Airlines, or American Airlines to get the fastest option. The distance from Kentucky to Chicago is about 287 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Kentucky to Chicago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $49. Southwest flights start at $49 while deals on Allegiant Air start at $66 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl and Louisville Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Japan Airlines (97%), Qatar Airways (96%), Republic Airways( 89%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $890 for a flight from Kentucky to Chicago. The cheapest flight overall is $91 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $91.

  • Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

    Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

  • Can I find deals for business class flights from Kentucky to Chicago?

    Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $73). Flying from Kentucky to Chicago in July is currently the most expensive (average of $139). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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LaGuardia to St. Louis flights
Boston to Midway flights

Top 4 airlines flying from Kentucky to Chicago

Discover the top 4 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$270FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$253FlexibilityNo cancel feeOn-time63%
ContourCheapest$116Average$154FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$122Average$283FlexibilityNo cancel feeOn-time69%

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